Waterfront holiday rentals in Siesta Key

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Siesta Key

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Superhost

Home in Longboat Key

4.88 out of 5 average rating, 120 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

Superhost

Apartment in Bradenton

5 out of 5 average rating, 3 reviews

Intracoastal Connections-Incredible Sunsets-Luxury

Experience waterfront luxury at this stunning 3-bed, 3-bath gem in Marina Walk, One Particular Harbor. Just 1.8 miles from Anna Maria Island's beaches, this home offers breathtaking views of Anna Maria Sound. Monthly guests enjoy resort pools, fitness center, nature trails, kayaking, and Sky Bar. Short-term visitors access the pool, splash park, and BBQ areas. Relax on the lanai, savor sunsets, or explore local attractions. Fully equipped with beach essentials, it’s your perfect coastal escape!

Top guest favourite

Home in Port Charlotte

5 out of 5 average rating, 21 reviews

Modern Waterfront Bliss

Bring the whole family to this exceptional canalfront gateway with lots of room for fun. Brand new, spacious retreat nestled along the peaceful canal. This modern home is designed for both comfort and style, offering cozy interiors and expansive living spaces perfect for relaxation. Whether you're enjoying the serene water views from the patio, cooking in the fully equipped kitchen, or unwinding in the beautifully appointed bedrooms, every corner of this house invites you to feel right at home.

Top guest favourite

Home in Bradenton

5 out of 5 average rating, 41 reviews

Dreamy Waterfront Bungalow w/Heated Spa. Near AMI.

Charming WATERFRONT retreat on Warner’s Bayou with a private boat dock right outside your door. Enjoy stunning waterfront views and frequent visits from dolphin and manatees. The fully equipped kitchen, spacious living area, and cozy bedrooms will make you feel right at home. Unwind on the patio or soak in the heated swim spa. Explore Robinson Preserve or take a short drive to Anna Maria Island for sun, sand, and adventure—just minutes away. Your unforgettable Florida escape starts here!

Superhost

Home in Port Charlotte

4.89 out of 5 average rating, 9 reviews

#1 Amazing Waterfront Home w/pool - Prime Location

Beautifully fully furnished waterfront home with pool, dock, and all the amenities! You'll enjoy the private, screened lanai with room to dine next to the pool with cascading fountain or soak up the sun in the lounge chairs while viewing the canal. Sleeps 6 comfortably. Gorgeous spacious master bedroom with master bath, two walk-in closets, jacuzzi tub and walk-in shower. Close to many restaurants, shopping, fishermen's Village and all Punta Gorda and Port Charlotte has to offer.

Guest favourite

Holiday home in Ruskin

4.94 out of 5 average rating, 51 reviews

No Damage Waterfront Townhome at Little Harbor

Come enjoy yourself at our townhome. Relax with the whole family at this peaceful place to stay with four private balconies. Our townhome is located in the seaside village of Little Harbor with a white sand secluded beach, two waterfront restaurants, seaside pool, tennis courts, fishing piers, watersports rentals, two onsite marinas, and much more. Enjoy watching the fish jump and the many varieties of birds in the natural preserve framed by the canal from your private balconies.

Top guest favourite

Townhouse in Ruskin

4.93 out of 5 average rating, 106 reviews

Still Waters Townhome, Sunrise and Sunset Views

Elegant home with 4 balconies, 2 overlooking water. Sunset and sunrise views. Gourmet kitchen, granite countertops, cooktop range, stainless steel appliances. Coffee maker, tea kettle, Nutra-bullet, toaster and more. Each room has a large flat screen smart TV. Bright, modern, immaculate. Wireless internet, Ethernet and Netflix. Washer and dryer on main level. Five minute walk to white sand private beach, complimentary umbrella and chairs. No smoking, no pets, no events.

Guest favourite

Apartment in St. Petersburg

4.89 out of 5 average rating, 118 reviews

Waterfront Condo w/ heated pool- near Fort Desoto

100+ raving reviews! This waterfront condo features a private balcony nestled next to the mangroves and shoreline with breathtaking water views. There is a full kitchen, king bed, a queen memory foam pullout sofa all waiting for you to enjoy. The resort like complex is located in the well desired Tierra Verde and features a waterfront heated pool and hot tub, observation pier, boat dock, and more! Only a short drive from Fort Desoto, Pass-A-Grille, and St. Pete Beach.

Superhost

Home in Ruskin

4.89 out of 5 average rating, 35 reviews

Waterfront Home w/ guest house!

Relax with the whole family at a peaceful waterfront vacation house w/ a separate guest house! This is a retreat to relax, & soak up the sun! Enjoy a pool table, dart board, putting green, kayaks, pool & hot tub while listening to the sound of a cascading waterfall. This spacious property is on a canal just outside the nature preserve & Tampa Bay. Your own boat ramp & two boat docks! 30-min drive to Tampa & St Petersburg, with many beaches nearby!

Guest favourite

Cottage in Ruskin

4.91 out of 5 average rating, 113 reviews

Little Manatee River Cottage

This cottage is located on the Little Manatee River. Sun City Center 10 min Aquatic rentals walking distance. The cottage is updated. Abundant fishing charters, Little Harbor, manatee viewing center and Simmons Park all within minutes. Fully furnished, linens, kitchen utensils; bath towels; blankets pillows comfy furnishings. View sunsets out on the river, on the dock or at Little Harbor sipping your favorite drink.

Superhost

Flat in Ruskin

4.8 out of 5 average rating, 10 reviews

The Inn at Little Harbor

Welcome to The Inn at Little Harbor—a perfect waterfront retreat! Enjoy a private beach, two pools, outdoor seating, and a grill. Relax with stunning sunsets, kayak, fish, or explore nearby attractions and restaurants. This serene getaway is ideal for families, couples, or solo travelers. Create lasting memories in this blend of relaxation and adventure. We can’t wait to host you in this charming destination!

Top guest favourite

Cottage in Bradenton

4.96 out of 5 average rating, 106 reviews

Waterfront*3bd 2ba*Pool* PingPong Table*relaxing

• Fish from dock • Dog Friendly • 2 bd / 2 ba • Keyless Entry • Fire Table • Pool and pool floats • Putting Green • Selfie Wall **Add my listing to you wishlist by clicking the 🖤 in the upper-right corner* >> 10 miles to beach, *Award Winning Ana Maria Island >>7 miles to IMG Academy >> 11 miles to SRQ Airport >>2 miles from Pittsburg Pirates Training camp